It's F. Scott Fitzgerald in drag. He was the prettiest girl in the show.
The photos were taken in 1916 to help promote The Evil Eye at Princeton's Triangle Club. Fitzgerald was in his third year at Princeton when the musical-comedy troupe performed the bawdy lyrics penned by the future Great Gatsby writer. In a review of his performance, the Times referred to Fitzgerald as "the most beautiful" girl in the whole production.
In 1924 when Fitzgerald's wife Zelda had an affair with a French aviator she reported that, in comparison, Fitzgerald was "inadequate." Ernest Hemingway, one of his many drinking buddies, included a passage inA Moveable Feastabout the size of Fitzgerald's penis, and gossips whispered that although Fitzgerald had a scorn for "fairies" he himself may have had homosexual experiences. To Zelda he once wrote, "The nearest I ever came to leaving you was when you told me you thought I was a fairy in the Rue Palatine," for she had accused him of having a relationship with Hemingway.
Of Hemingway, Fitzgerald had once written, "I really loved him, but of course it wore out like a love affair. The fairies have spoiled all that," implying that their friendship had stopped because of such gossip. Sheliah Graham (Fitzgerald's mistress), according to his biographer Jeffrey Meyers, knew about the relative sizes of penises, however, and "she found the tubercular, drug-addicted and often alcoholic Fitzgerald a creditable performer – 'very satisfactory . . . in terms of giving physical pleasure.' After lovemaking, they would lie happily in each other's arms for a long time."
The homosexual gossip continued, however, despite his describing homosexuals unscientifically as "Nature's attempt to get rid of soft boys by sterilizing them."
Critic Sally Eckhoff, reviewing two of Matthew J. Bruccoli's books, Fitzgerald and Hemingway: A Dangerous Friendship (1994) and F. Scott Fitzgerald: A Life in Letters (1994), notes, "From all the evidence now available, we can safely believe Hemingway's assertion that Mrs. Fitzgerald had told her husband that his dick was too small. During a drunken lunch at Michaud's, the distraught Scott spilled the beans to Ernest [Hemingway - both repaired to the hommes room to size up the problem. " 'Forget what Zelda said,' I told him. 'Zelda is crazy,' " Hemingway wrote in his chapter called "A Matter of Measurements." (According to Edmund Wilson, Hemingway tried to dilute Scott's anguish about his penis by claiming 'it only seemed to him small because he looked at it from above. You have to look at in a mirror.' Fitzgerald didn't buy it.) Hemingway complained to Max Perkins that 'almost every bloody fool thing I have ever seen or known him to do has been directly or indirectly Zelda inspired,' but added, 'I would not have Scott imagine I believed this for the world.' "
In Tender is the Night, Fitzgerald tries to give his opinion of homosexuality in the characters of the Real family, though they are not the only gay men mentioned in the book. The main protagonist, Dick Diver (a psychoanalyst) is sent to examine a case which involves a corrupt Spanish nobleman, Real, whose son Francisco is a homosexual. The father wants his son to be "cured." Fitzgerald here is echoing a common attitude both of his time and ours — that is, homosexuality is illness or a perversion of "natural" heterosexual love. It need hardly be noted that the heterosexual relationships in this novel are, without exception, failures; if they are "natural," they are no happier than the "unnatural" ones depicted in Book III.
The father of Francisco, however, has been so adamant about making his son conform to his idea of normalcy that he has forced him to make a tour of bordellos. The inhumanity of such an act has two dimensions — that of forcing the young man, against his will, to perform sexually, and, equally as degrading, the assumption that the prostitution of females is somehow natural and healthy. When the boy was not cured by the experience, Senor Real was reduced to lashing him with a whip. The homosexuality seems, to Dick, an incurable sickness, and the father's cruelty a sexual perversion as well.